Microsoft's new Outlook mail is a welcome Hotmail replacement

Outlook mail
The all-new Outlook mail service from Microsoft (labeled "NewMail" in its pre-launch format) replaces Hotmail as a real 21st-century webmail service.

If you're one of the millions of people who are embarrassed to admit that you still have a Hotmail address, your day has come. Seriously, you can migrate to Microsoft's impressive new Outlook email service, and start using its smart services to merge your contacts with Facebook and clean out all the newsletter spam that has built up over the last 1,000 years.

OK, OK, yes, you're saying ... "Outlook? But I already have Outlook. It's an app. On my computer." Well, you can blame Microsoft for confusing things by using the name of their popular email and calendar client as the name of their new service that offers ... email and calendar. But don't let it stress you out. At least you can put your Outlook email service into your Outlook app!

As a Gmail, Hotmail and erstwhile Yahoo mail user, I am sufficiently impressed by what Microsoft has cooked up here, a mail service that will soon mercifully replace the aging Hotmail as the default webmail for Microsoft's Live service. It's called Outlook, and that means you can get an address (today, in fact). You can keep your old Hotmail address too, and even add other aliases — completely separate email addresses that route to certain folders — to hand out to retailers and other would-be spammers.

Some of the top features are available in the current Hotmail and in comparable form on Gmail and other emails, but what makes this whole thing so nice is its interface, and how so much of the smart stuff happens automatically, or at least semi-automatically. 

Outlook mail
Mail is automatically categorized, but you can add other incoming notes to categories, too.

Right after you migrate your Hotmail account to Outlook, all those machine-generated newsletters, shipping updates and social updates get readily categorized, for your filing or deletion. Anything with attached documents or attached photos is also called out in a special "quick view" category.

You can very easily apply rules by individual address, a selection of them, or a whole folder or "quick view" category. The main filters, under the Sweep menu, are:

  • Move all from… - Puts every received email from sender into a designated folder, and offers to do the same with future emails.
  • Delete all from… - Deletes every received email from sender, and offers to do the same with future emails.
  • Schedule cleanup - Lets you choose how long you want emails from a given sender to sit in your inbox before they're automatically moved or deleted. (As someone who is bad at cleaning out the inbox, I love this option!)
cleanup Outlook mail
Scheduling clean ups is the best way to deal with all that semi-relevant spam, like weekly notes from your favorite retailers.

It may come as no surprise to people who have been watching the development of Windows 8 and Windows Phone that your former Hotmail contacts, along with contacts from Facebook, Twitter, LinkedIn, even Gmail, can be merged into a big ole database labeled People. This is the same People database that is accessible throughout Microsoft's products, so users of Windows Phone, for instance, are basically already set up for Outlook mail — they just have to log in.

People social
In the People contacts page, you can write on people's Facebook walls, tweet at them, and even send direct messages.

The social integration doesn't stop there. You can quickly jump on a live chat with someone using Facebook (alternatively, of course, you can use Windows Live Messenger). And when you click on an email from somebody you are Facebook friends with, or who you follow on Twitter, their status appears to the right of the note. And if you're not a friend or follower of them? You can quickly remedy that shortcoming with a click.

The interface itself is clean and butter smooth, with very nice contextual menus that pop up when you need them, one-click read/unread buttons that show up on rollover, drag-and-drop contact info and more. I have yet to see an ad, but when they do appear, they will be (for the time being) shoved off to the far right, in a gutter, which alternately becomes the social update display when you are viewing emails of friends, and a messaging window when you're actively chatting with someone.

Microsoft tells me that the data mined by the Outlook mail service won't go as deep as others, so while ads served will be contextual, they will only be based on the subjects and (name brand) senders of email, rather than on the actual contents of email, which may get more personal. 

At a technical level, smartphone power users may be delighted to know that this new email service is based on Exchange Active Sync which means that when you set it up as a mail account on your iPhone, BlackBerry or other device, you can get push updates, and as more features roll out, treat it as a bonafide Exchange account (but one that's free).

SkyDrive web interface
The new SkyDrive interface is well worth a look all by itself, especially since SkyDrive offers integration across many operating systems.

The Outlook mail service is the heart of a major revamp of all of the Live services, and when you sign up for a new account or migrate your Hotmail account to it (by clicking on the Options button), you will see a new People contacts manager and a fresh new SkyDrive interface as well. The Calendar portion of the service is not yet updated, so don't get too mad when it feels a bit crusty by comparison.

Yes, Outlook mail is a work in progress. I've experienced lots of hiccups, particularly surrounding the integration with Facebook and Twitter. It is, after all, in beta and likely to be there for a while. Once Microsoft gets the kinks ironed out, though, and gets a healthy population using it, the plan is to phase out the painfully antiquated Hotmail for good. 

As someone who only touches his Hotmail with the proverbial 10-foot pole, but who has spent an unnatural amount of time over the past few days inside Outlook mail, running smart email filters, watching with glee as a ridiculous amount of old mail gets flushed away, I welcome the change, and applaud Microsoft for doing some real Web innovation here.

Where do you get this new email? Just head over to, or log into your Hotmail and click on the Options button. 

Wilson Rothman is the Technology & Science section editor at Catch up with him on Twitter at @wjrothman, and join our conversation on Facebook.